##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-07-05
_journal_date_accepted     2011-07-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      8
_journal_page_first     o2176
_journal_page_last     o2176
_journal_paper_category     QO
_journal_coeditor_code     PV2428
_publ_contact_author_name     'K. Sethusankar'
_publ_contact_author_address
;
   Department of Physics
   RKM Vivekananda College (Autonomous)
   Chennai - 600 004
   India.
;
_publ_contact_author_email     'ksethusankar@yahoo.co.in'
_publ_contact_author_fax     '044 091 2499 3057'
_publ_contact_author_phone     '044 091 24484170'
_publ_section_title
;
2-[(4-Formylphenyl)(hydroxy)methyl]acrylonitrile
;
loop_
    _publ_author_name
    _publ_author_address
    'C. M. Sai Prasanna'
;
Department of Physics
Ethiraj College for Women
Chennai 600 008
India
;
    'K. Sethusankar'
;
Department of Physics
RKM Vivekananda College (Autonomous)
Chennai 600 004
India
;
    'R. Rajesh'
;
Department of Organic Chemistry
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'R. Raghunathan'
;
Department of Organic Chemistry
University of Madras
Guindy Campus
Chennai 600 025
India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-[(4-Formylphenyl)(hydroxy)methyl]acrylonitrile
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H9 N O2'
_chemical_formula_sum     'C11 H9 N O2'
_chemical_formula_iupac     'C11 H9 N O2'
_chemical_formula_weight     187.19
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     7.6089(5)
_cell_length_b     6.0895(3)
_cell_length_c     20.5135(14)
_cell_angle_alpha     90.00
_cell_angle_beta     93.615(2)
_cell_angle_gamma     90.00
_cell_volume     948.59(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2778
_cell_measurement_theta_min     1.99
_cell_measurement_theta_max     30.14
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.311
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     392
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12108
_diffrn_reflns_av_R_equivalents     0.0252
_diffrn_reflns_av_sigmaI/netI     0.0196
_diffrn_reflns_theta_min     1.99
_diffrn_reflns_theta_max     30.14
_diffrn_reflns_theta_full     30.14
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -28
_diffrn_reflns_limit_l_max     28
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     2778
_reflns_number_gt     2109
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0600
_refine_ls_R_factor_gt     0.0448
_refine_ls_wR_factor_gt     0.1252
_refine_ls_wR_factor_ref     0.1370
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.037
_refine_ls_number_reflns     2778
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.1498P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.199
_refine_diff_density_min     -0.208
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.29788(17) 1.2762(2) 0.08969(7) 0.0530(3) Uani d . 1 1 . .
    H H1 0.2060 1.2372 0.1152 0.064 Uiso calc R 1 1 . .
    C C2 0.45120(15) 1.1299(2) 0.09117(6) 0.0402(3) Uani d . 1 1 . .
    C C3 0.59636(15) 1.17738(19) 0.05636(6) 0.0403(3) Uani d . 1 1 . .
    H H3 0.5982 1.3042 0.0312 0.048 Uiso calc R 1 1 . .
    C C4 0.73929(15) 1.03554(19) 0.05910(6) 0.0377(3) Uani d . 1 1 . .
    H H4 0.8374 1.0683 0.0361 0.045 Uiso calc R 1 1 . .
    C C5 0.73630(14) 0.84482(18) 0.09612(5) 0.0341(2) Uani d . 1 1 . .
    C C6 0.58917(16) 0.7961(2) 0.12973(6) 0.0440(3) Uani d . 1 1 . .
    H H6 0.5855 0.6670 0.1538 0.053 Uiso calc R 1 1 . .
    C C7 0.44760(16) 0.9386(2) 0.12758(6) 0.0473(3) Uani d . 1 1 . .
    H H7 0.3496 0.9059 0.1507 0.057 Uiso calc R 1 1 . .
    C C8 0.88910(15) 0.68441(19) 0.09921(6) 0.0386(3) Uani d . 1 1 . .
    H H8 0.8530 0.5530 0.0742 0.046 Uiso calc R 1 1 . .
    C C9 0.94025(16) 0.6160(2) 0.16879(6) 0.0416(3) Uani d . 1 1 . .
    C C10 0.9246(2) 0.4136(2) 0.19036(8) 0.0658(4) Uani d . 1 1 . .
    H H10A 0.9592 0.3799 0.2335 0.079 Uiso calc R 1 1 . .
    H H10B 0.8788 0.3045 0.1625 0.079 Uiso calc R 1 1 . .
    C C11 1.01071(18) 0.7847(2) 0.21163(7) 0.0499(3) Uani d . 1 1 . .
    N N1 1.0657(2) 0.9196(3) 0.24571(8) 0.0783(4) Uani d . 1 1 . .
    O O1 0.28115(14) 1.44271(18) 0.05813(6) 0.0647(3) Uani d . 1 1 . .
    O O2 1.03273(12) 0.77961(17) 0.07008(5) 0.0550(3) Uani d . 1 1 . .
    H H2 1.1103 0.6874 0.0670 0.083 Uiso calc R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0386(6) 0.0578(8) 0.0626(8) 0.0154(6) 0.0044(6) -0.0036(6)
    C2 0.0328(5) 0.0454(6) 0.0420(6) 0.0090(4) -0.0012(4) -0.0055(5)
    C3 0.0394(6) 0.0378(6) 0.0434(6) 0.0073(4) -0.0005(5) 0.0030(5)
    C4 0.0336(5) 0.0409(6) 0.0390(6) 0.0055(4) 0.0047(4) 0.0040(4)
    C5 0.0326(5) 0.0371(5) 0.0326(5) 0.0067(4) 0.0007(4) -0.0005(4)
    C6 0.0402(6) 0.0457(6) 0.0466(7) 0.0051(5) 0.0073(5) 0.0104(5)
    C7 0.0337(6) 0.0579(7) 0.0512(7) 0.0058(5) 0.0099(5) 0.0057(6)
    C8 0.0390(6) 0.0381(5) 0.0389(6) 0.0101(4) 0.0055(4) 0.0029(4)
    C9 0.0417(6) 0.0405(6) 0.0426(6) 0.0102(5) 0.0018(5) 0.0033(5)
    C10 0.0954(12) 0.0465(8) 0.0535(8) 0.0048(8) -0.0100(8) 0.0109(6)
    C11 0.0546(7) 0.0469(7) 0.0476(7) 0.0105(6) -0.0009(6) 0.0022(5)
    N1 0.0984(12) 0.0638(8) 0.0706(9) 0.0003(8) -0.0120(8) -0.0121(7)
    O1 0.0556(6) 0.0605(6) 0.0781(7) 0.0279(5) 0.0057(5) 0.0043(5)
    O2 0.0419(5) 0.0599(6) 0.0653(6) 0.0204(4) 0.0195(4) 0.0194(5)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.2055(18) ?
    C1 C2 . 1.4664(16) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.3829(17) ?
    C2 C7 . 1.3853(18) ?
    C3 C4 . 1.3871(15) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.3887(15) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.3835(16) ?
    C5 C8 . 1.5168(14) ?
    C6 C7 . 1.3818(17) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 O2 . 1.4036(15) ?
    C8 C9 . 1.5139(16) ?
    C8 H8 . 0.9800 ?
    C9 C10 . 1.3173(18) ?
    C9 C11 . 1.4338(18) ?
    C10 H10A . 0.9300 ?
    C10 H10B . 0.9300 ?
    C11 N1 . 1.1410(19) ?
    O2 H2 . 0.8200 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 C2 . . 125.37(14) ?
    O1 C1 H1 . . 117.3 ?
    C2 C1 H1 . . 117.3 ?
    C3 C2 C7 . . 119.84(10) ?
    C3 C2 C1 . . 121.51(12) ?
    C7 C2 C1 . . 118.64(12) ?
    C2 C3 C4 . . 119.92(11) ?
    C2 C3 H3 . . 120.0 ?
    C4 C3 H3 . . 120.0 ?
    C3 C4 C5 . . 120.20(11) ?
    C3 C4 H4 . . 119.9 ?
    C5 C4 H4 . . 119.9 ?
    C6 C5 C4 . . 119.58(10) ?
    C6 C5 C8 . . 118.90(10) ?
    C4 C5 C8 . . 121.50(10) ?
    C7 C6 C5 . . 120.20(11) ?
    C7 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    C6 C7 C2 . . 120.24(11) ?
    C6 C7 H7 . . 119.9 ?
    C2 C7 H7 . . 119.9 ?
    O2 C8 C9 . . 110.75(10) ?
    O2 C8 C5 . . 109.36(9) ?
    C9 C8 C5 . . 111.56(9) ?
    O2 C8 H8 . . 108.4 ?
    C9 C8 H8 . . 108.4 ?
    C5 C8 H8 . . 108.4 ?
    C10 C9 C11 . . 120.17(13) ?
    C10 C9 C8 . . 123.43(12) ?
    C11 C9 C8 . . 116.39(11) ?
    C9 C10 H10A . . 120.0 ?
    C9 C10 H10B . . 120.0 ?
    H10A C10 H10B . . 120.0 ?
    N1 C11 C9 . . 179.54(16) ?
    C8 O2 H2 . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C3 . . . . 1.9(2) ?
    O1 C1 C2 C7 . . . . -177.02(14) ?
    C7 C2 C3 C4 . . . . -1.32(18) ?
    C1 C2 C3 C4 . . . . 179.80(11) ?
    C2 C3 C4 C5 . . . . 0.69(18) ?
    C3 C4 C5 C6 . . . . 0.66(17) ?
    C3 C4 C5 C8 . . . . 178.94(10) ?
    C4 C5 C6 C7 . . . . -1.38(19) ?
    C8 C5 C6 C7 . . . . -179.71(11) ?
    C5 C6 C7 C2 . . . . 0.8(2) ?
    C3 C2 C7 C6 . . . . 0.60(19) ?
    C1 C2 C7 C6 . . . . 179.52(12) ?
    C6 C5 C8 O2 . . . . -171.48(11) ?
    C4 C5 C8 O2 . . . . 10.23(15) ?
    C6 C5 C8 C9 . . . . -48.61(15) ?
    C4 C5 C8 C9 . . . . 133.09(11) ?
    O2 C8 C9 C10 . . . . -122.89(15) ?
    C5 C8 C9 C10 . . . . 115.05(15) ?
    O2 C8 C9 C11 . . . . 56.40(14) ?
    C5 C8 C9 C11 . . . . -65.67(14) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O2 H2 O1 1_645 0.82 1.99 2.8107(15) 175